Catalyst-free C–H bond halogenation/imidation of N-heterocycles

Abstract

The application of N-halosuccinimides (NXS) as “nucleophilic” nitrogen sources in organic transformations represents an emerging and promising area of research. This work utilized the two key intermediates – X-radicals and N-radicals – generated synchronously upon homolysis of NXS, achieving the simultaneous construction of C–X bonds (halogenation) and C–N bonds (imidation) on fused pyridine (Py) rings. Furthermore, through a subsequent hydrazinolysis step integrated into the same reaction system, a one-pot synthesis of amino halogenated isoquinoline derivatives can be effectively achieved. The method is concise and efficient, as the transformation proceeds smoothly without requiring the addition of any metal catalysts, photocatalysts, or additional oxidants.